Pittsboro Homes with Association Pool

Welcome to Pittsboro, North Carolina—a charming town nestled in the heart of Chatham County. Known for its rich history, scenic landscapes, and a close-knit community, Pittsboro offers a unique blend of small-town charm and modern conveniences. With its picturesque downtown area, featuring local shops, delightful eateries, and vibrant community events, residents enjoy a lifestyle that’s both relaxed and engaging.

One of the standout features of living in Pittsboro is the availability of homes with association pools. Imagine spending warm summer days lounging by the pool, enjoying a refreshing swim, or hosting gatherings with friends and family in a serene environment. These community amenities foster a sense of belonging and provide a perfect backdrop for creating lasting memories.

Pittsboro is also conveniently located near the beautiful Jordan Lake, offering residents ample opportunities for outdoor activities such as hiking, fishing, and boating. The town’s proximity to the bustling cities of Chapel Hill and Raleigh ensures that you can enjoy the tranquility of small-town life while still having easy access to urban amenities, including shopping, dining, and cultural attractions.

Whether you’re a first-time homebuyer or looking to settle into a peaceful retreat, Pittsboro’s homes with association pools provide the ideal setting for relaxation and recreation. Embrace the warmth and hospitality of this delightful town, where community spirit thrives, and your dream home awaits. Come and experience the charm of Pittsboro—your oasis in North Carolina!

Newest Pittsboro Homes with Association Pool

$599,900

2 Beds ⋅ 2 Baths ⋅ 10187353 MLS ⋅ ACTIVE Status

Elegance meets everyday comfort in The Carroway, a floor plan designed to make every day feel effortless. At its heart is a glamorous kitchen, anchored by a multi-function island and opening onto sunlit living and dining spaces — perfect for cooking, entertaining, or simply gathering together. The Owner's Retreat offers a true escape, featuring an en suite bathroom and spacious walk-in closet for a private, restorative haven. A well-appointed guest room with its own bathroom ensures visitors enjoy comfort and privacy of their own. Step outside to the covered porch, an inviting extension of the home ideal for quiet evenings or lively gatherings with friends and family.

39 Englehart Ct, Pittsboro

$549,999

3 Beds ⋅ 3 Baths ⋅ 10185428 MLS ⋅ ACTIVE Status

Experience timeless elegance in this immaculate French Provincial-style home, thoughtfully designed and meticulously maintained. Built in 2010, this stunning residence offers three spacious bedrooms, two-and-a-half bathrooms, a generous bonus room, an elegant formal dining room, and a charming breakfast area. The luxurious main-level primary suite provides a private retreat, while beautiful hardwood floors flow throughout the main living spaces. A screened-in porch creates the perfect setting for relaxing or entertaining. Enjoy access to the neighborhood pool and an exceptional location just minutes from historic downtown Pittsboro, dining, shopping, and more.

28 Old Post Ct, Pittsboro

$600,600

2 Beds ⋅ 2 Baths ⋅ 10178970 MLS ⋅ ACTIVE Status

Welcome to the Sweetfern, a thoughtfully designed home where warm, inviting finishes meet effortless everyday living. The heart of the home features an upgraded cooktop kitchen with warm wood tones, elegant touches of green, and brushed brass accents that create a sophisticated yet comfortable feel. The open-concept family room is highlighted by impressive 12' sliding glass doors, bringing in abundant natural light and creating a seamless connection to the outdoor living space. A private enclosed study with French doors offers the perfect space for a home office, reading room, or flex space. Retreat to the spacious Owner's Suite, enhanced by an elegant tray ceiling, while the mudroom adds everyday functionality with a utility sink and countertop. With its beautiful blend of warmth, style, and carefully selected upgrades, this Sweetfern is designed to feel welcoming from the moment you step inside. Encore at Chatham Park offers a maintenance-free, resort-inspired lifestyle with lawn care included and exclusive access to a 5,200-square-foot clubhouse, fitness center, pickleball and tennis courts, resort-style pool and spa, putting green, walking trails, and a full-time Lifestyle Director who keeps the community active and connected. The model home is located at 175 Prospect Place and open Monday through Saturday from 10:00 am -6:00 pm and Sunday 12:00 pm - 6:00 pm. This home has not started construction, however the structural details are already firm. Design upgrades were added as of 8/17/26 reflecting the recent increase in listing price.

87 Englehart Ct, Pittsboro

$965,000

4 Beds ⋅ 4 Baths ⋅ 10084591 MLS ⋅ ACTIVE Status

Beautiful custom home in the highly desirable Chapel Ridge neighborhood. The primary suite and guest bedroom are on the first floor with two additional bedrooms upstairs. This wonderful open floor plan gives you plenty of room to entertain. Walking distance to the many community amenities including the pool, golf and tennis.

829 Chapel Ridge Dr, Pittsboro

$1,200,000

4 Beds ⋅ 4 Baths ⋅ 10161024 MLS ⋅ ACTIVE Status

A rare opportunity awaits in the exclusive Estates at Chapel Ridge. This distinguished Prewitt-Douglas custom home sits on nearly an acre -- one of the last remaining lots in this coveted enclave. Spanning over 3,500 square feet, the residence showcases high-end finishes throughout and a desirable main-level primary suite complete with dual walk-in closets. Four bedrooms and 3.5 baths offer ample space for comfortable everyday living and effortless entertaining. Residents enjoy access to Chapel Ridge's full suite of community amenities, providing year-round recreation for the entire family. Exceptional craftsmanship, a premier lot, and an unmatched location -- opportunities like this are few and far between.

36 Rosefield Ct, Pittsboro

$1,285,000

4 Beds ⋅ 4 Baths ⋅ 10161265 MLS ⋅ ACTIVE Status

Exceptional Prewitt-Douglas custom home situated on a quiet cul-de-sac in the prestigious Chapel Ridge community. This 4 bedroom, 3.5 bath residence boasts an open, expansive floor plan designed for effortless entertaining -- both indoors and out. Thoughtfully crafted with generous living spaces and outstanding attention to detail throughout. Residents enjoy access to world-class community amenities including golf, tennis, and a resort-style pool. A rare opportunity to own a distinguished home in one of the area's most coveted neighborhoods -- this one will not last.

64 Mist Wood Ct, Pittsboro

$1,230,000

4 Beds ⋅ 9 Baths ⋅ 10159657 MLS ⋅ ACTIVE Status

Exceptional Prewitt-Douglas custom home overlooking Chapel Ridge golf course. This 3,365 SF residence offers 4 bedrooms, 4.5 baths, a 2-car garage, and a dedicated golf viewing room ideal for entertaining. Quality craftsmanship throughout with sweeping golf course views. A rare find in a premier setting -this one won't last long.

227 Deep Crk, Pittsboro

$824,900

3 Beds ⋅ 3 Baths ⋅ 10165069 MLS ⋅ ACTIVE Status

Set on one of the most coveted homesites in Encore at Chatham Park, this exceptional residence offers refined, single-level living at its finest. The largest single level ''Moorefield'' model in the community, the home spans approximately 2,668 square feet and is enhanced by a thoughtfully added 175-square-foot flex or craft room, providing both elegance and versatility. Designed with a keen eye for detail, the home features three spacious bedrooms and three beautifully appointed full bathrooms. The dining room is anchored by a sophisticated Valor fireplace, creating a warm yet elevated ambiance ideal for entertaining. The gourmet kitchen is a true centerpiece, showcasing upgraded cabinetry, a custom designer backsplash, striking countertops, and an impressive 10-foot chestnut oak hardwood-wrapped island--perfect for gatherings both intimate and grand. Outdoors, the property is equally captivating. Lush, meticulously curated landscaping graces both the front and rear grounds, complemented by a charming stone wall that enhances the home's distinguished presence. A mature, fruit-bearing fig tree adds a rare and delightful touch, completing this one-of-a-kind offering in one of Pittsboro's most desirable communities.

33 Imagine Way, Pittsboro

$955,000

4 Beds ⋅ 4 Baths ⋅ 10132755 MLS ⋅ ACTIVE Status

Exceptional custom home in the sought-after Chapel Ridge community. This thoughtfully designed 4 bedroom, 4 bath residence offers an ideal layout with a main-level primary suite and secondary bedroom, perfect for single-level convenience. The open-concept living area flows seamlessly into a beautifully appointed kitchen, creating an inviting space for everyday living and entertaining. Upstairs, two additional bedrooms each feature private en suite baths, while a bonus room and flexible flex space provide endless possibilities for work, play, or relaxation. All of this set within Chapel Ridge -- a premier community offering resort-style amenities just moments from your door. A rare combination of thoughtful design, quality craftsmanship, and an unmatched lifestyle.

191 High Ridge Ln, Pittsboro

$1,595,000

4 Beds ⋅ 4 Baths ⋅ 10160197 MLS ⋅ ACTIVE Status

Wow! This gorgeous 4070 sf Prewitt-Douglas Custom home located in Chapel Ridge Estates sits on a rare one and one half acre lot. Featuring 4 bedrooms, 3.5 bathrooms, a fabulous hearth room and 3 car garage, this one will be truly stunning.

60 Willow Creek Ct, Pittsboro

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Listings provided courtesy of Triangle MLS, Inc. of NC, Internet Data Exchange Database. Information deemed reliable but not guaranteed. © 2026 Triangle MLS, Inc. of North Carolina. Data last updated .